


The Five Times Dean Struggled in School and the One Time He Didn’t

by Strength_in_pain



Series: John and his boys [28]
Category: Supernatural
Genre: Dean Winchester throughout the years, Gen, High School Student Dean Winchester, Kid Dean Winchester, Kindergarten Dean Winchester, Sad Dean Winchester, Sad and Happy, Student Dean Winchester, Young Dean Winchester
Language: English
Status: In-Progress
Published: 2019-01-18
Updated: 2019-01-18
Packaged: 2019-10-12 07:16:41
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,319
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17463038
Author URL: https://archiveofourown.org/users/Strength_in_pain/pseuds/Strength_in_pain
Summary: A Young Dean Winchester’s view on school throughout the years.





	1. Chapter 1

**Author's Note:**

> I really like this one. It’s mainly about Dean though. Sorry to any Sammy lovers. 
> 
> This is the story on how Dean learned over the years to view school.
> 
> (Sorry about the 1st page. I don’t know how to show you guys pics. :( oh well. Just hit the next chapter to get to the story. Again I apologize.)

 Pic


	2. Chapter 2

> **The fives times Dean struggled in School and the one time he didn’t.**

 

Oklahoma.  

Dean 5, Sam 1 

 

“Hold your pencil like this.” Dean’s kindergarten teacher was the prettiest woman alive, well, other than Mommy. But Dean barely remembers his mommy. He looks at pictures of her every night to keep her blue eyes in his mind. 

 

But Mrs. Lois was so sweet like Mommy. When she spoke to Dean, she always wore a smile and she usually praised him for writing his letters really well. She was sitting on the floor next to his tiny kindergarten chair, smiling as he traced the letters. 

 

“Very good, Dean! You’re doing wonderful.” Dean’s big, wide, innocent eyes grew the size of saucers. He was beaming from the praise. Eager to get another compliment, Dean worked really hard on his letters. He was going to memorize the alphabet in no time. Then he would be a big kid. And everyone knows big kids are smart. 

 

“Okay class. I want you to keep practicing your letters at home with mommy and daddy.” 

 

“Yes Mrs. Lois.” The kids chorused. 

 

Dean waited patiently with Mrs. Lois for his Dad to show up. But Dad doesn’t usually come, instead Kelly picks him up. Miss Kelly was a maid at the motel where Dean now lived. It wasn’t the same as home, but Daddy said they could never go back home, so Dean doesn’t talk about it. 

 

Miss Kelly walked Dean to the room where Daddy was and Dean jumped on his bed. He threw his arms around the man, chatted his ear off, and showed him all the gold stars he got. Daddy praised Dean too, which was even better than Mrs. Lois praising him. Dean loved school. He loved it.

                         _______________

 

Mrs. Fletcher was Dean’s first grade teacher. She was just as nice as Mrs. Lois. Her class was really fun because they had story time and snack time. 

 

“All right boys and girls. I want everyone to sit quietly in your seats.”

 

Dean was the first to sit down. He had been playing tag with a bunch of kids but Mrs. Fletcher told them to sit, so he had to sit. All of the other boys and girls were running around chasing each other, squealing and screaming. Even when Mrs. Fletcher got them all to sit down, they were still talking. 

 

Dean was sitting quietly, with his hands folded in front of him just like Mrs. Fletcher taught him on the first day of class. Daddy thought it was very respectful to sit like that too. 

 

Mrs. Fletcher looked angry, Dean noticed. He started fidgeting nervously. Hopefully Mrs. Fletcher wouldn’t yell.

 

 “Right now.” She said sternly, “The only person ready for second grade is Dean.” 

 

A big smile broke out on Dean’s face. His teacher was proud of him. He noticed from the corner of his eye a few kids looking at him and whispering. 

 

Mrs. Fletcher walked over to him and handed him a chocolate chip cookie. “Good boys and girls who follow the rules get extra cookies.” She winked at him, then went back to the front of the class. That cookie tasted so good, Dean thought he was in heaven. 

 

Until they were walking to the bus and Dustin, the line leader, wouldn’t let Dean stand beind him. 

 

“You should stand with Mrs. Fletcher, teachers pet.” 

 

Dean furrowed his eyebrows, “What?”

 

“You’re a teacher’s pet. You know, a kiss up.”

 

“No I’m not.” Dean whined. 

 

“Yes you are.”

 

“No I’m not.”

 

“Yes you are.” 

 

Dad picked him up in his 1967 black Chevy impala. He was in a good mood, listening to Don’t Stop Believing by Journey. But Dean didn’t want to sing along.

 

“Hey Dean? You okay?” Dad asked as he parked the impala in a hotel parking lot. 

 

“Yes sir.” 

 

John sighed, “we talked about this. You don’t need to call me sir all the time. Right now, I’m just Daddy okay?” 

 

“Dad.” 

 

“Sure. Okay. Dad.” He nodded, and took Dean by the shoulders and steered him to the impala’s hood. 

 

“You wanna work on Baby with me? We can fix her up real good.”

 

“Sammy.” 

 

“Sammy’s with Fred. Come on, you help me with the car.” 

 

Fred was a hunter Dad worked with a few times. He scared Dean because he never smiled, ever. 

 

“Okay.” Dean whispered, as he reached up for his father to carry him. John obliged and put Dean on his hip. He leaned over the car and started pointing things out. It amazed John how much information his kids could absorb. Dean seemed to soak up everything he said like a sponge. Still, his boy was quiet, reserved. Something was wrong. 

 

“How was school?” 

 

“I don’t wanna talk about it.” Dean mumbled, hiding his face into John’s shirt. 

 

“Hey, come on now. Was it that bad?” 

 

“Nobody wants to be my friend anymore.” Dean sniffled, and John knew the first signs of crying when he heard it. 

 

“Shhhh.” He kissed his son’s soft wrinkle-free forehead. “What happened?”

 

“Dustin said I’m a teacher’s pet. But I was just following the rules, Dad! It’s not my fault Mrs. Fletcher gave me an extra cookie.” 

 

“Those kids are just Jealous, ace. You got rewarded for being good. I bet they wish they would’ve been good too.”

 

“Why do they have to take it out on me.” Dean asked, now pulling his face away from his Father’s shoulder. 

 

“Because kids are mean. I don’t know why, but I know it’s not the first time you’ll experience this. But I’ll tell you what, Dean. You shouldn’t let anything they say affect you. The only opinions you should care about are ones from the people that you love.”   

 

Slipping his arms around his father’s neck, Dean gave him a big hug. The hug was returned, but then Dad was setting him down. 

 

“Come on, let’s wash her.” 

 

Dean helped his Dad fill buckets of soapy water and together they sprayed off Baby, cleaning the car until it sparkled. 

 

“Gotcha!” Dean cried in surprise when the soapy water hit his head. 

 

“Dad!” He screamed while running after Dad all across the parking lot. He tackled him to the ground, although John might have purposefully laid down on the ground, but Dean felt like he tackled his dad, and then he poured water on his face. 

 

                        _______________ 

 

“The sky is not green.” Mrs. Larch said, putting her hands on her hips. This was Dean’s fourth, first grade teacher. He moved a lot this year which means he had a lot of different schools and teachers. But Mrs. Larch was one of the worst. She never let Dean play how he wanted or color what he wanted. 

 

“Well I think the sky is green and the grass is blue.” Dean said, going back to coloring. Molly was handing him more crayons and Dean thanked her, grabbing the purple one. 

 

“Clouds are not purple.” The teacher scolded. “You are such a sarcastic little kid. You know clouds are white.” 

 

“He’s just pretending.” Molly whispered, giving Dean a love-sick puppy look. He was pretty sure she had a crush on him. But girls were scary and totally off limits. Dad said he had to be careful around girls. He isn’t allowed to hit any of them unless they are monsters. And not just the phrase, ‘oh she’s being a monster,’ but like, an actual bone crushing, blood slurping, monster. Dean has yet to encounter that in the first grade, so he knows not to hit any of these girls. But Dad said the boys were fair game. 

 

“Dean. I said stop coloring inappropriately.” Mrs. Larch took his sheet of paper away and gave him a new one. “Start over.” 

 

Dean nodded, grabbed the green crayon and started coloring the sky. Mrs. Larch’s face burned a bright red color. “Are you purposefully trying to disobey me?” 

 

“No ma’am. I’m just coloring how I want.” 

 

“I think it’s neat!” Steve said. 

 

“Yeah, he’s funny.” Marcus added. 

 

“I said to color properly or you won’t color at all.” Mrs. Larch threatened. 

 

Dean’s jaw set. He grabbed the blue crayon and with determination, and scribbled the grass a dark shade of ocean blue. 

 

“That’s it.” Mrs. Larch yelled. She strode over to Dean’s chair and yanked him up by the wrist. 

 

“You want to be disrespectful and rude. You can sit in the corner.” 

 

Tears were threatening to spill out of Dean’s eyes. The closer he got to the corner, the more he struggled, trying to get out of Mrs. Larch’s grip. 

 

“You sit right here.” She said, pushing him down on the tiny blue chair. He gulped, looking up at her with pleading eyes. “And don’t move.” 

 

He watched as she walked away, then he turned to face forward, looking at the stupid wall. He could actually hear his own heart beating, which made him slightly nervous. Why was he so afraid? It was just a dumb wall. But Dean felt isolated and embarrassed. He had never felt so small. That is, until Mrs. Larch addressed the whole class and said, “This is what happens when you don’t follow rules.”

 

Dean stomach lurched. Why did she have to point it out to the whole class? _What, did she wake up and say, let’s just make poor little Dean’s day miserable._

_“_ Do you want to end up like Dean?” She asked the class. 

 

“No Mrs. Larch.” The class responded miserably. 

 

“Was Dean good today?” 

 

“No Mrs. Larch.”

 

“Then don’t disobey your elders like Dean did. Is that clear?” 

 

“Yes Mrs. Larch.” 

 

Dean was sobbing. He didn’t even care if stupid Mrs. Larch saw. He didn’t care if he looked like a wimp. All he wanted was to go home and be with Sammy. His little brother was so lucky he didn’t have to go to school yet. If Dean could help it, he was going to try and stop Sammy from going to school. 

 

Dean thinks God might have heard his prayers after all because ten minutes later there’s a knock on the door and Dean hears his Dad’s voice. 

 

“Hi, I’m sorry. An emergency came up at home. I need to take my kid out of school.” John said kindly. 

 

“You’ll have to ask the secretary. She’ll give you a paper to fill out.” 

 

John’s face twisted dangerously. “May I please see my son.” 

 

“Not until 3:00. He’s being punished. If you would like to see him before then, please contact the secretary.” 

 

John peered in the classroom to see his son sitting in the corner shoulders shaking. It’s at that moment something inside of John Winchester snapped and he completely lost his cool. 

 

“Son of a bitch.” He whispered under his breath then, at the top of his lungs he screamed, “What kind of fucking teacher are you! What kind of Goddamn mother fucking school is this!” He rushed past her, storming into the classroom in his muddy boots and dirty shirt. 

 

“Excuse me, sir. But what do you think you’re doing.” Mrs. larch shouted. “This is a classroom. You’re scaring the kids.” 

 

“I’m taking my son.” John growled. He got to the corner and lifted Dean gently by the arm. His boy was crying, clinging to his shirt tightly. 

 

“This is an outrage.” Mrs. Larch yelled. “I’m going to call security.” 

 

“You do that.” John screamed. “I’m going down to the principals myself. We’ll have a nice little chat about your teaching methods. ‘Can’t see my son till three.’ What kind of bull shit is that? I can’t see my own son. The kid I raised since he came out of my wife’s womb! The kid I took care of every fucking day before this stupid school shit. And now, I can’t see him before three. I don’t think so.” John’s face was tomato red, veins popping all over his forehead. There were a bunch of children crying. One little girl hid under her desk, but Dean felt so safe, so protected right then. He loved his father, his hero. 

 

“Come on, Dean. We’re leaving. You’re never coming back here again.” 

 

“Good. Our school doesn’t ever want to see your family again, Mr. Winchester.” 

 

“Good riddance.” John screamed, slamming the door behind him. 

 

He took Dean to the bathroom so he could cool off, and throw some water on his face. Once John’s blood pressure had returned to normal he crouched down and pulled Dean into a giant hug. 

 

“Shhh. It’s okay.” John whispered into his son’s soft hair. “It’s okay. It’s all over now.” 

 

Dean’s crying slowly faded into the thin bathroom walls and soon he was just sniffling, holding his face with his hands. 

 

“I’m sorry.” Dean hiccuped turning away. 

 

“You have nothing to be sorry for.” 

 

                          _____________

 

Dean’s in another first grade class. He likes his teacher, Mr. K. because he lets the kids listen to music and play instruments. Today was arts and crafts day. 

 

“I want you to be as creative as possible. Paint a beautiful picture of a sunny day. But make it about yourself. So if you like candy, make the candy rain from the sky.” 

 

Dean stared at his sheet of paper, then carefully dipped his paint brush in the blue paint. As gently as he could, he pained the sky blue and the grass green. 

 

“Excellent job, Abbey. Nice, Taylor. Dean -“ Mr. K paused. He looked down at the paper with a sad smile, “Dean, this is very nice. But where’s the creativity?” 

 

“No creativity. The sky is blue and the grass is green. Those are the facts.” 

 

Mr. K. signed. “Okay, Dean. Go hang it on the wall.” 

 

A week passed and John was called in for a parent teacher conference with Dean in the room. 

 

“He’s a smart boy but he won’t apply himself. He won’t write down his numbers. He won’t read when I call on him. He won’t even play with the other kids at recess. Honestly, I’m worried about him, Mr. Winchester.” 

 

“Dean I want you to promise Mr. K. You will try.”

 

Dean glanced at his father sadly, almost pleadingly. But John held his own steady gaze. 

 

Finally Dean gave in, “I promise I’ll try harder.” He whispered. 

 

                     ___________________

 

“This is so stupid! What’s the point.” Dean screamed, throwing his textbook across the mini motel room. Luckily, John ducked just in time to avoid getting hit. 

 

“You just bought yourself a week of no TV, do you understand me.” John screamed. He was at his wits end. 

 

The twelve year old sat up straight and nodded. “Yes sir.” 

 

“Good. Now do you want to tell me what’s got you so worked up?” 

 

“It’s this stupid homework assignment.” Dean cried. “I don’t understand what the fuck letters are doing in math!” 

 

“Watch your mouth.” John said, pointing a dangerous finger at him. 

 

“A bunch of kids at school say it.” Sam piped in from behind the couch. 

 

“Well you’re not one of them. And I don’t want to hear that word out of either of your mouths or I’ll wash it out with soap, clear?” 

 

“But Dad -“

 

“Sam, get your ass back in bed.” John snapped. Any one else would realize they should back off by now but not Sam.

 

“Hey just because Dean’s throwing a fit doesn’t mean you can take your anger out on me.” 

 

Dean stood up so fast his chair flew back and slammed against the floor. Sam’s eyes grew wide, and he quickly ran to his bedroom, Dean hot on his tail. 

 

John grabbed Dean’s waist and kept him from killing his little brother. “Settle down. Come on. Finish this crap so we can go to bed.” 

 

After fifteen minutes of his Dad breathing down his neck, Dean couldn’t take it anymore. He snapped his pencil in frustration, pounding his fist into his school books until his knuckles turned bloody. 

 

“What the hell is wrong with you?” John screamed frustrated at his son’s antics. 

 

“Everything!” Dean exclaimed miserably. “I can’t do this. I don’t get it. And I hate it. I fucking hate it.” 

 

John’s response was a crisp clean smack right across Dean’s cheek. His son was gasping, clutching his mouth with his hand.

 

“What did I just say?” John asked, but Dean was breaking down. 

 

“Dad.” He whimpered, trying to control his voice. At this age, Dean was a pro at stopping himself from crying. “I’m not smart enough.” His voice broke off and a few tears dribbled down his cheek. 

 

“Yes you are.” John said with a very long sigh. He grabbed Dean’s hands in his own. “Of course you are.” 

 

“No I’m not.” Dean said, looking at the floor. “But it’s okay because hunters don’t need to know math anyway, right? And that’s what I’m going to be when I grow up. So I don’t need school.” 

 

“A general education is a good thing to have and you will graduate high school, young man.” 

 

“Dad.” Dean whined more tears spilling out his eyes. 

 

“No. I want you to. Your mom would want you to.” John said, feeling his throat tighten. During moments like these he wished Mary was there. 

 

“Come on. Open your books. I’ll help you. I got a GED a long time ago. I should be able to help a little.” He said softly, fingers gently brushing over the red mark on Dean’s cheek. 

 

 

                     ____________________

 

“Dean Winchester. It’s a pleasure. Sit down.” Principal Warren said. 

 

Dean rolled his eyes, then plopped down in the hard wooden chair. He gave a tiny smirk, then threw his feet up on the principal’s desk. 

 

“So, what did I do this time?” Dean asked. 

 

“Get your feet off my table, boy.” Dean sighed, but dragged his feet off. 

 

“For someone who is only sixteen, you have quite the record.” The principal said, throwing a cream colored envelope on the desk. 

 

“What can I say?” Dean shrugged, “I move around a lot. Every school has a different rule, it’s hard to keep up.” 

 

“Shall we go over some of your misbehavior your teacher’s have complained about this past week?” 

 

“Do I have a choice?” 

 

“Being a class clown, stealing iron and sodium from the chemistry lab, kissing under the bleachers, skipping classes, destruction of property, and my all time favorite, fighting.” 

 

“Right. I personally didn’t think it was so much a fight but more so a minor disagreement. We were discussing some thing and it got out of hand.” Dean said, looking down at his hands. “Look, you already called my Dad. What more do you want to do?” 

 

“I’m not here to lecture you, Dean.” 

 

Dean scoffed, “sure feels that way.” 

 

“I just want to talk.” The principal said. 

 

“You sound like my brother.” 

 

“You’re a very smart kid, Dean. If you just applied yourself -“

 

“I could stay out of jail, yeah, I’ve heard this speech before Mr. Warren.” 

 

Pulling open the desk drawer, Mr. Warren handed Dean a few college applications. 

 

“When you’re in detention, I want you think about applying, ok?” 

 

Dean’s warm eyes stared blankly at the suited man. He cautiously picked up the applications as if they were made of glass. Briefly, Dean glanced over the variety of different choices and schools. 

 

“You have a lot of potential, Dean. Please don’t throw it away by picking fights and making jokes.” 

 

Dean stood up, extended his hand and waited for the principal to shake it. “Thank you, sir. Are we done here?” 

 

“Yes. You can go back to class.” 

 

Dean smiled, half-heartedly, then walked into the hallway. He dropped the applications in a nearby trashcan, then pushed open the cafeteria doors, flipping his Science teacher off on his way to his lonely table. 

 

College. Yeah right. If Dean wasn’t smart enough for high school there was no way he was going to college. Besides, Dean hated school. He hated it. 


End file.
